3-Fucosyllactose

3-Fucosyllactose (3-FL) is a purified, white to off-white powder that is a type of human milk oligosaccharide (HMO) and a trisaccharide composed of D-galactose, D-glucose, and L-fucose.

• Abbreviation: 3-FL
• IUPAC Name: β-D-Galactopyranosyl-(1→4)-[α-L-fucopyranosyl-(1→3)]-D-glucopyranose
• Molecular Formula: C18H32O15
• Molecular Mass: 488.44 g/mol
• CAS Number: 41312-47-4

Chemical and Structural Description

• Structure: 3-FL consists of a lactose backbone (D-galactose and D-glucose) with an L-fucose residue attached at position 3 of the glucose via an α-(1-3) glycosidic bond.
• Physical Properties: It is highly purified (≥ 90% by weight in commercial preparations) and appears as a crystalline or agglomerated powder. Other saccharides such as D-lactose, L-fucose, D-galactose, and D-glucose may be present in minor amounts (<5%).
• Source: 3-FL is either extracted from human milk or produced industrially via microbial fermentation using genetically modified Escherichia coli strains.

Biological and Functional Context

• Occurrence: 3-FL is naturally present in human breast milk and is structurally identical to its synthetic counterpart.
• Classification: It belongs to the family of human milk oligosaccharides (HMOs), known for their prebiotic, immune-modulating, and anti-adhesion roles in infant nutrition.
• Functional Role: 3-FL supports the development of beneficial gut microbiota, enhances immune responses, and may protect against certain pathogens in infants.

Analytical Confirmation

• Structural Analysis: Its molecular structure and purity are confirmed by advanced spectroscopic techniques like 1H-NMR, 13C-NMR, and 2D-NOESY analyses, ensuring equivalence between the novel food ingredient and natural 3-FL.

Specification Table

Related Compounds

1. 2′-Fucosyllactose (2′-FL): A constitutional isomer, differing in the position of fucose attachment (α‑(1–2) to galactose instead of α‑(1–3) to glucose). 3-Fucosyllactose is used in food supplements and infant formulae to replicate the beneficial functions of HMOs found naturally in human milk.
2. https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=OJ%3AL_202302210
3. https://pubchem.ncbi.nlm.nih.gov/compound/161460
4. https://www.food.gov.uk/research/research-projects/safety-assessment-outcome-of-the-assessment-of-3-fucosyllactose-3-fl-as-a-novel-food
5. https://commonchemistry.cas.org/detail?cas_rn=41263-94-9
6. https://pmc.ncbi.nlm.nih.gov/articles/PMC9131588/
7. https://pubchem.ncbi.nlm.nih.gov/compound/Fucosyllactose
8. http://science.food.gov.uk/article/131970-safety-assessment-of-3-fucosyllactose-3-fl-as-a-novel-food-for-use-in-food-and-food-supplements-rp2001
9. https://pubchem.ncbi.nlm.nih.gov/compound/122560-33-2
10. https://www.sciencedirect.com/topics/chemistry/3-fucosyllactose
11. https://pubchem.ncbi.nlm.nih.gov/compound/16216990